JP2010535722A5 - - Google Patents
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- JP2010535722A5 JP2010535722A5 JP2010519351A JP2010519351A JP2010535722A5 JP 2010535722 A5 JP2010535722 A5 JP 2010535722A5 JP 2010519351 A JP2010519351 A JP 2010519351A JP 2010519351 A JP2010519351 A JP 2010519351A JP 2010535722 A5 JP2010535722 A5 JP 2010535722A5
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- cycloalkyl
- ring
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006709 (C5-C7) cycloalkenyl group Chemical group 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
Description
[式中、
Zは、
(CH2)m(m=0、1または2);
(CH2)nO(n=1、2または3);
O(CH2)p(p=0、1、2または3);
CH2SO2;
CHNR6;
CH2NR6;
NR6(R6は、H、または直鎖状もしくは分枝状(C1〜C4)アルキルである);
OCOR4R5;および
CR4R5
からなる群から選択され、式中、
R4は独立に、H、または(C1〜C4)シクロアルキルで場合によって置換されている直鎖状もしくは分枝状(C1〜C4)アルキル、好ましくはメチルから選択され、
R5は独立に、直鎖状または分枝状(C1〜C4)アルキル、好ましくはメチル;フェニル;ベンジル;NH2;およびHNCOOR’(R’は、直鎖状または分枝状(C1〜C4)アルキル、好ましくはt−ブチルである)からなる群から選択され、
R1およびR2は異なるかまたは同じであり、独立に、
−H;
−(C3〜C7)シクロアルキルまたは(C5〜C7)シクロアルケニルから選択された1個または複数の置換基で場合によって置換されている直鎖状または分枝状(C1〜C6)アルキル;
−(C3〜C7)シクロアルキル;
−(C5〜C7)シクロアルケニル;
−直鎖状または分枝状(C2〜C6)アルケニル;および
−直鎖状または分枝状(C2〜C6)アルキニル
からなる群から選択され、
R3は、H、CN、NO2、CF3、およびハロゲン原子からなる群から独立に選択された1個または複数の置換基であり、
Aは、環系、すなわちアリール、(C3〜C8)シクロアルキル、またはヘテロアリールなど飽和、部分不飽和、または不飽和とすることができる単環式または二環式の環であり、前記環系Aは5〜10個の環原子を有し、少なくとも1個の環原子はヘテロ原子(例えば、N、S、またはO)であり、A環系上の場合による置換基RXは、1個または複数とすることができ、同じでも異なってもよく、独立に、
−1個または複数の(C3〜C7)シクロアルキルで場合によって置換されている直鎖状または分枝状(C1〜C6)アルキル;
−1個または複数の(C3〜C7)シクロアルキルで場合によって置換されている直鎖状または分枝状(C2〜C6)アルケニル;
−1個または複数の(C3〜C7)シクロアルキルで場合によって置換されている直鎖状または分枝状(C2〜C6)アルキニル;
−(C5〜C7)シクロアルケニル;
−フェニル;
−(C3〜C7)ヘテロシクロアルキル;
−OR7(R7は、H;1個または複数の(C3〜C7)シクロアルキルで場合によって置換されている(C1〜C10)アルキル;(C3〜C7)シクロアルキル;(C1〜C4)アルキレン−(C3〜C7)ヘテロシクロアルキル;CO(C1〜C6)アルキル;−COO(C1〜C6)アルキル;−フェニル;−ベンジル;−(C1〜C10)アルキル−NR8R9(R8およびR9は独立に、H、直鎖状または分枝状(C1〜C6)アルキルからなる群から選択され、これらは、結合している窒素原子と一緒に、飽和環、部分飽和環、または不飽和環を形成し、好ましくはNR8R9は(C1〜C10)アルキルに結合して、例えば飽和、部分飽和、または不飽和のピペリジン環、オキサジン環、イミダゾール環を形成し、これらの環は、(C1〜C4)アルキルで場合によって置換されている)、からなる群から選択される;および
−ハロゲン原子;
−CN;
−NO2;
−NR10R11(R10およびR11は、異なるかまたは同じであり、かつ独立に、
−H;
−フェニルまたは(C3〜C7)シクロアルキルで場合によって置換されている直鎖状または分枝状(C1〜C6)アルキル;
−COC6H5;
−CO−(C1〜C4)アルキル;
−COO−(C1〜C4)アルキル;
−CONH−(C1〜C6)アルキル−R12(R12は、
−H;
−(C1〜C4)アルキル;
−OR4R5からなる群から選択される);および
−CONH(C1〜C4)アルキル−N(C1〜C4)アルキル
からなる群から選択され、
あるいは、これらは、結合している窒素原子と一緒に、飽和または部分飽和環、好ましくはピペリジル環を形成する;
−(C1〜C4)アルキル−NR10R11;
−COR12(R12は、フェニル、または直鎖状もしくは分枝状(C1〜C6)アルキルである);
−オキソ;
−HNSO2R13(R13は、(C1〜C4)アルキル、またはハロゲン原子もしくは(C1〜C4)アルキル基で場合によって置換されているフェニルである);
−SO2R14(R14は、(C1〜C4)アルキル、OH、またはNR10R11であり、R10およびR11は上記に定義した通りである);
−SOR15(R15は、フェニルまたは(C1〜C4)アルキルである);
−SR16(R16は、H、フェニルまたは(C1〜C4)アルキルである);
−COOR17(R17は、H、(C1〜C4)アルキル、フェニルまたはベンジルである);および
−(CH2)qOR18(q=1、2、3または4、かつR18は、Hまたは(C1〜C4)シクロアルキルである);
からなる群から選択される]
ならびにその薬学的に許容される塩およびそのピリジン環のN−オキシドを対象とする。
[Where:
Z is
(CH 2 ) m (m = 0, 1 or 2);
(CH 2 ) n O (n = 1, 2, or 3);
O (CH 2 ) p (p = 0, 1, 2, or 3);
CH 2 SO 2 ;
CHNR 6 ;
CH 2 NR 6 ;
NR 6 (R 6 is H, or linear or branched (C 1 -C 4 ) alkyl);
OCOR 4 R 5 ; and CR 4 R 5
Selected from the group consisting of:
R 4 is independently, H, or (C 1 ~C 4) linear optionally substituted with cycloalkyl or branched (C 1 ~C 4) alkyl, preferably selected from methyl,
R 5 is independently linear or branched (C 1 -C 4 ) alkyl, preferably methyl; phenyl; benzyl; NH 2 ; and HNCOOR ′ (R ′ is linear or branched (C 1 to C 4 ) alkyl, preferably t-butyl)
R 1 and R 2 are different or the same, independently
-H;
Linear or branched (C 1 -C) optionally substituted with one or more substituents selected from-(C 3 -C 7 ) cycloalkyl or (C 5 -C 7 ) cycloalkenyl. 6 ) alkyl;
- (C 3 ~C 7) cycloalkyl;
- (C 5 ~C 7) cycloalkenyl;
- linear or branched (C 2 ~C 6) alkenyl; - is selected from linear or branched (C 2 ~C 6) the group consisting of alkynyl, and
R 3 is one or more substituents independently selected from the group consisting of H, CN, NO 2 , CF 3 , and halogen atoms;
A is a ring system, ie a monocyclic or bicyclic ring that can be saturated, partially unsaturated, or unsaturated, such as aryl, (C 3 -C 8 ) cycloalkyl, or heteroaryl, Ring system A has 5 to 10 ring atoms, at least one ring atom is a heteroatom (eg, N, S, or O), and the optional substituent R X on the A ring system is Can be one or more and can be the same or different, independently
-1 or more (C 3 ~C 7) linear optionally substituted with cycloalkyl, or branched (C 1 ~C 6) alkyl;
-1 or more (C 3 ~C 7) linear optionally substituted with cycloalkyl, or branched (C 2 ~C 6) alkenyl;
-1 or more (C 3 ~C 7) linear optionally substituted with cycloalkyl, or branched (C 2 ~C 6) alkynyl;
- (C 5 ~C 7) cycloalkenyl;
-Phenyl;
- (C 3 ~C 7) heterocycloalkyl;
—OR 7 (R 7 is H; (C 1 -C 10 ) alkyl optionally substituted with one or more (C 3 -C 7 ) cycloalkyl; (C 3 -C 7 ) cycloalkyl; (C 1 -C 4 ) alkylene- (C 3 -C 7 ) heterocycloalkyl; CO (C 1 -C 6 ) alkyl; -COO (C 1 -C 6 ) alkyl; -phenyl; -benzyl; 1 -C 10 ) alkyl-NR 8 R 9 (R 8 and R 9 are independently selected from the group consisting of H, linear or branched (C 1 -C 6 ) alkyl, which are bonded Together with the nitrogen atom forming a saturated, partially saturated or unsaturated ring, preferably NR 8 R 9 is bonded to (C 1 -C 10 ) alkyl, for example saturated, partially saturated, or Unsaturated piperidine ring, oxazine ring Forming an imidazole ring, which rings are optionally substituted with (C 1 -C 4 ) alkyl); and a halogen atom;
-CN;
-NO 2;
—NR 10 R 11 (where R 10 and R 11 are different or the same and are independently
-H;
- phenyl or (C 3 ~C 7) like straight-chain, optionally substituted with a cycloalkyl or branched (C 1 ~C 6) alkyl;
-COC 6 H 5;
-CO- (C 1 ~C 4) alkyl;
-COO- (C 1 ~C 4) alkyl;
-CONH- (C 1 -C 6 ) alkyl-R 12 (R 12 is
-H;
- (C 1 ~C 4) alkyl;
Selected from the group consisting of —OR 4 R 5 ); and —CONH (C 1 -C 4 ) alkyl-N (C 1 -C 4 ) alkyl;
Alternatively, they together with the nitrogen atom to which they are attached form a saturated or partially saturated ring, preferably a piperidyl ring;
- (C 1 ~C 4) alkyl -NR 10 R 11;
-COR 12 (R 12 is phenyl, or linear or branched (C 1 -C 6 ) alkyl);
-Oxo;
-HNSO 2 R 13 (R 13 is (C 1 -C 4 ) alkyl, or phenyl optionally substituted with a halogen atom or a (C 1 -C 4 ) alkyl group);
-SO 2 R 14 (R 14 is (C 1 -C 4 ) alkyl, OH, or NR 10 R 11 , R 10 and R 11 are as defined above);
-SOR 15 (R 15 is phenyl or (C 1 -C 4) alkyl);
-SR 16 (R 16 is, H, phenyl or (C 1 -C 4) alkyl);
-COOR 17 (R 17 is H, (C 1 -C 4 ) alkyl, phenyl or benzyl); and-(CH 2 ) q OR 18 (q = 1, 2, 3 or 4 and R 18 is , H or (C 1 -C 4 ) cycloalkyl);
Selected from the group consisting of]
And pharmaceutically acceptable salts thereof and N-oxides of the pyridine ring.
Claims (1)
Zは、
(CH2)m(m=0、1、または2);
(CH2)nO(n=1、2、または3);
O(CH2)p(p=0、1、2、または3);
CH2SO2;
CHNR6;
CH2NR6;
NR6(R6は、H、または直鎖状もしくは分枝状(C1〜C4)アルキルである);
OCOR4R5;および
CR4R5
からなる群から選択され、式中、
R4は独立に、H、または(C1〜C4)シクロアルキルで場合によって置換されている直鎖状もしくは分枝状(C1〜C4)アルキル、好ましくはメチルから選択され、
R5は独立に、直鎖状または分枝状(C1〜C4)アルキル、好ましくはメチル;フェニル;ベンジル;NH2;およびHNCOOR’(R’は、直鎖状または分枝状(C1〜C4)アルキル、好ましくはt−ブチルである)からなる群から選択され、
R1およびR2は異なるかまたは同じであり、独立に、
H;
(C3〜C7)シクロアルキルまたは(C5〜C7)シクロアルケニルから選択された1個または複数の置換基で場合によって置換されている直鎖状または分枝状(C1〜C6)アルキル;
(C3〜C7)シクロアルキル;
(C5〜C7)シクロアルケニル;
直鎖状または分枝状(C2〜C6)アルケニル;および
直鎖状または分枝状(C2〜C6)アルキニル
からなる群から選択され、
R3は、H、CN、NO2、CF3、およびハロゲン原子からなる群から独立に選択された1個または複数の置換基であり、
Aは、環系、すなわちアリール、(C3〜C8)シクロアルキル、またはヘテロアリールなど飽和、部分不飽和、または不飽和とすることができる単環式または二環式の環であり、前記環系Aは5〜10個の環原子を有し、少なくとも1個の環原子はヘテロ原子(例えば、N、S、またはO)であり、A環系上の場合による置換基RXは、1個または複数とすることができ、同じでも異なってもよく、独立に、
1個または複数の(C3〜C7)シクロアルキルで場合によって置換されている直鎖状または分枝状(C1〜C6)アルキル;
1個または複数の(C3〜C7)シクロアルキルで場合によって置換されている直鎖状または分枝状(C2〜C6)アルケニル;
1個または複数の(C3〜C7)シクロアルキルで場合によって置換されている直鎖状または分枝状(C2〜C6)アルキニル;
(C5〜C7)シクロアルケニル;
フェニル;
(C3〜C7)ヘテロシクロアルキル;
OR7(R7は、H;1個または複数の(C3〜C7)シクロアルキルで場合によって置換されている(C1〜C10)アルキル;(C3〜C7)シクロアルキル;(C1〜C4)アルキレン−(C3〜C7)ヘテロシクロアルキル;CO(C1〜C6)アルキル;COO(C1〜C6)アルキル;フェニル;ベンジル;(C1〜C10)アルキル−NR8R9(R8およびR9は独立に、H、直鎖状または分枝状(C1〜C6)アルキルからなる群から選択され、R8およびR9は、これらが結合している窒素原子と一緒に、飽和環、部分飽和環、または不飽和環を形成し、好ましくはNR8R9は(C1〜C10)アルキルに結合して、例えば飽和、部分飽和、または不飽和のピペリジン環、オキサジン環、イミダゾール環を形成し、これらの環は、(C1〜C4)アルキルで場合によって置換されている、からなる群から選択される);および
ハロゲン原子;
CN;
NO2;
NR10R11(R10およびR11は、異なるかまたは同じであり、かつ独立に、
H;
フェニルまたは(C3〜C7)シクロアルキルで場合によって置換されている直鎖状または分枝状(C1〜C6)アルキル;
COC6H5;
CO−(C1〜C4)アルキル;
COO−(C1〜C4)アルキル;
CONH−(C1〜C6)アルキル−R12(R12は、
H;
(C1〜C4)アルキル;
OR4R5からなる群から選択される);および
CONH(C1〜C4)アルキル−N(C1〜C4)アルキル
からなる群から選択され、
あるいは、R10およびR11は、これらが結合している窒素原子と一緒に、飽和または部分飽和環、好ましくはピペリジル環を形成する;
(C1〜C4)アルキル−NR10R11;
COR12(R12は、フェニル、または直鎖状もしくは分枝状(C1〜C6)アルキルである);
オキソ;
HNSO2R13(R13は、(C1〜C4)アルキル、またはハロゲン原子もしくは(C1〜C4)アルキル基で場合によって置換されているフェニルである);
SO2R14(R14は、(C1〜C4)アルキル、OH、またはNR10R11であり、R10およびR11は上記に定義した通りである);
SOR15(R15は、フェニルまたは(C1〜C4)アルキルである);
SR16(R16は、H、フェニルまたは(C1〜C4)アルキルである);
COOR17(R17は、H、(C1〜C4)アルキル、フェニルまたはベンジルである);および
(CH2)qOR18、式中、q=1、2、3または4、かつR18は、Hまたは(C1〜C4)シクロアルキルである);
からなる群から選択される]
ならびにその薬学的に許容される塩およびそのピリジン環のN−オキシド。
Compound of general formula (I)
Z is
(CH 2 ) m (m = 0, 1, or 2);
(CH 2 ) n O (n = 1, 2, or 3);
O (CH 2 ) p (p = 0, 1, 2, or 3);
CH 2 SO 2 ;
CHNR 6 ;
CH 2 NR 6 ;
NR 6 (R 6 is H, or linear or branched (C 1 -C 4 ) alkyl);
OCOR 4 R 5 ; and CR 4 R 5
Selected from the group consisting of:
R 4 is independently, H, or (C 1 ~C 4) linear optionally substituted with cycloalkyl or branched (C 1 ~C 4) alkyl, preferably selected from methyl,
R 5 is independently linear or branched (C 1 -C 4 ) alkyl, preferably methyl; phenyl; benzyl; NH 2 ; and HNCOOR ′ (R ′ is linear or branched (C 1 to C 4 ) alkyl, preferably t-butyl)
R 1 and R 2 are different or the same, independently
H;
Linear or branched (C 1 -C 6) optionally substituted with one or more substituents selected from (C 3 -C 7 ) cycloalkyl or (C 5 -C 7 ) cycloalkenyl. ) Alkyl;
(C 3 ~C 7) cycloalkyl;
(C 5 ~C 7) cycloalkenyl;
Is selected from the group consisting and linear or branched (C 2 ~C 6) alkynyl; linear or branched (C 2 ~C 6) alkenyl
R 3 is one or more substituents independently selected from the group consisting of H, CN, NO 2 , CF 3 , and halogen atoms;
A is a ring system, ie a monocyclic or bicyclic ring that can be saturated, partially unsaturated, or unsaturated, such as aryl, (C 3 -C 8 ) cycloalkyl, or heteroaryl, Ring system A has 5 to 10 ring atoms, at least one ring atom is a heteroatom (eg, N, S, or O), and the optional substituent R X on the A ring system is Can be one or more and can be the same or different, independently
Linear or branched (C 1 -C 6 ) alkyl optionally substituted with one or more (C 3 -C 7 ) cycloalkyl;
One or more (C 3 ~C 7) linear optionally substituted with cycloalkyl, or branched (C 2 ~C 6) alkenyl;
One or more (C 3 ~C 7) linear optionally substituted with cycloalkyl, or branched (C 2 ~C 6) alkynyl;
(C 5 ~C 7) cycloalkenyl;
Phenyl;
(C 3 ~C 7) heterocycloalkyl;
OR 7 (R 7 is H; (C 1 -C 10 ) alkyl optionally substituted with one or more (C 3 -C 7 ) cycloalkyl; (C 3 -C 7 ) cycloalkyl; C 1 -C 4) alkylene - (C 3 ~C 7) heterocycloalkyl; CO (C 1 ~C 6) alkyl; COO (C 1 ~C 6) alkyl; phenyl; benzyl; (C 1 ~C 10) alkyl -NR 8 R 9 (R 8 and R 9 are independently, H, is selected from the group consisting of linear or branched (C 1 ~C 6) alkyl, R 8 and R 9, it is bonded Together with the nitrogen atom forming a saturated, partially saturated or unsaturated ring, preferably NR 8 R 9 is linked to (C 1 -C 10 ) alkyl, for example saturated, partially saturated, Or an unsaturated piperidine ring, Jin ring to form an imidazole ring, the rings, (C 1 -C 4) alkyl is optionally substituted with, is selected from the group consisting of); and halogen atoms;
CN;
NO 2 ;
NR 10 R 11 (R 10 and R 11 are different or the same and independently
H;
Linear or branched (C 1 -C 6 ) alkyl optionally substituted with phenyl or (C 3 -C 7 ) cycloalkyl;
COC 6 H 5 ;
CO- (C 1 ~C 4) alkyl;
COO- (C 1 ~C 4) alkyl;
CONH- (C 1 -C 6 ) alkyl-R 12 (R 12 is
H;
(C 1 ~C 4) alkyl;
Selected from the group consisting of OR 4 R 5 ); and CONH (C 1 -C 4 ) alkyl-N (C 1 -C 4 ) alkyl;
Alternatively, R 10 and R 11 together with the nitrogen atom to which they are attached form a saturated or partially saturated ring, preferably a piperidyl ring;
(C 1 ~C 4) alkyl -NR 10 R 11;
COR 12 (R 12 is phenyl or linear or branched (C 1 -C 6 ) alkyl);
Oxo;
HNSO 2 R 13 (R 13 is (C 1 -C 4 ) alkyl, or phenyl optionally substituted with a halogen atom or a (C 1 -C 4 ) alkyl group);
SO 2 R 14 (R 14 is (C 1 -C 4 ) alkyl, OH, or NR 10 R 11 , R 10 and R 11 are as defined above);
SOR 15 (R 15 is phenyl or (C 1 -C 4 ) alkyl);
SR 16 (R 16 is H, phenyl or (C 1 -C 4 ) alkyl);
COOR 17 (R 17 is H, (C 1 -C 4 ) alkyl, phenyl or benzyl); and (CH 2 ) q OR 18 , where q = 1, 2, 3 or 4, and R 18 Is H or (C 1 -C 4 ) cycloalkyl);
Selected from the group consisting of]
And pharmaceutically acceptable salts thereof and N-oxides of the pyridine ring.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP07114019A EP2022783A1 (en) | 2007-08-08 | 2007-08-08 | "Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors" |
PCT/EP2008/005843 WO2009018909A2 (en) | 2007-08-08 | 2008-07-17 | Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors |
Related Child Applications (1)
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JP2013212664A Division JP5746298B2 (en) | 2007-08-08 | 2013-10-10 | Derivatives of 1-phenyl-2-pyridinylalkyl alcohol as phosphodiesterase inhibitors |
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JP2010535722A JP2010535722A (en) | 2010-11-25 |
JP2010535722A5 true JP2010535722A5 (en) | 2011-08-25 |
Family
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JP2010519351A Ceased JP2010535722A (en) | 2007-08-08 | 2008-07-17 | Derivatives of 1-phenyl-2-pyridinylalkyl alcohol as phosphodiesterase inhibitors |
JP2013212664A Active JP5746298B2 (en) | 2007-08-08 | 2013-10-10 | Derivatives of 1-phenyl-2-pyridinylalkyl alcohol as phosphodiesterase inhibitors |
JP2015094698A Active JP6023846B2 (en) | 2007-08-08 | 2015-05-07 | Derivatives of 1-phenyl-2-pyridinylalkyl alcohol as phosphodiesterase inhibitors |
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JP2013212664A Active JP5746298B2 (en) | 2007-08-08 | 2013-10-10 | Derivatives of 1-phenyl-2-pyridinylalkyl alcohol as phosphodiesterase inhibitors |
JP2015094698A Active JP6023846B2 (en) | 2007-08-08 | 2015-05-07 | Derivatives of 1-phenyl-2-pyridinylalkyl alcohol as phosphodiesterase inhibitors |
Country Status (38)
Country | Link |
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US (7) | US7923565B2 (en) |
EP (3) | EP2022783A1 (en) |
JP (3) | JP2010535722A (en) |
KR (1) | KR101200683B1 (en) |
CN (1) | CN101796028B (en) |
AR (1) | AR068057A1 (en) |
AU (1) | AU2008286027B2 (en) |
BR (1) | BRPI0814065B8 (en) |
CA (1) | CA2695580C (en) |
CL (1) | CL2008002330A1 (en) |
CO (1) | CO6290760A2 (en) |
CY (2) | CY1117324T1 (en) |
DK (2) | DK2185515T3 (en) |
EA (1) | EA017530B1 (en) |
ES (2) | ES2563478T3 (en) |
GE (1) | GEP20125537B (en) |
HK (1) | HK1145686A1 (en) |
HR (2) | HRP20160292T1 (en) |
HU (2) | HUE027171T2 (en) |
IL (2) | IL203712A (en) |
JO (1) | JO3181B1 (en) |
LT (1) | LT2947068T (en) |
MA (1) | MA31586B1 (en) |
ME (1) | ME00974B (en) |
MX (1) | MX2010001544A (en) |
MY (1) | MY152692A (en) |
NO (1) | NO2947068T3 (en) |
NZ (1) | NZ583103A (en) |
PE (1) | PE20090698A1 (en) |
PL (2) | PL2947068T3 (en) |
PT (2) | PT2185515E (en) |
RS (2) | RS56765B1 (en) |
SI (2) | SI2947068T1 (en) |
TN (1) | TN2010000044A1 (en) |
TW (1) | TWI444366B (en) |
UA (1) | UA99622C2 (en) |
WO (1) | WO2009018909A2 (en) |
ZA (1) | ZA201000832B (en) |
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EP2216327A1 (en) * | 2009-02-06 | 2010-08-11 | CHIESI FARMACEUTICI S.p.A. | Benzoic acid (1-phenyl-2-pyridin-4-yl)ethyl esters as phosphodiesterase inhibitors |
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SG195319A1 (en) * | 2011-06-06 | 2013-12-30 | Chiesi Farma Spa | Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors |
CN103827088B (en) * | 2011-09-26 | 2017-10-13 | 奇斯药制品公司 | It is used as the derivative of the pyridyl alkyl alcohol of 1 phenyl 2 of phosphodiesterase inhibitors |
CN103889972A (en) * | 2011-10-21 | 2014-06-25 | 奇斯药制品公司 | Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors |
RU2637945C2 (en) * | 2012-06-04 | 2017-12-08 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Derivatives of 1-phenyl-2-pyridinyl-alkyl alcohols as phosphodiesterase inhibitors |
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PL3293176T3 (en) | 2013-10-22 | 2021-06-28 | Chiesi Farmaceutici S.P.A. | Crystal form of a pde4 inhibitor |
RU2016121852A (en) * | 2013-12-05 | 2017-12-07 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | DERIVATIVES OF BENZHYDRIL FOR THE TREATMENT OF RESPIRATORY DISEASES |
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